Allyl bromide → 1-Allylpiperazine

HRID 8933

Reaction equation

HRID 8933 reaction equation
F[C:2](F)(F)[C:3]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=O.[CH2:13](Br)C=C.C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH2:3]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)[CH:2]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 7172020Trifluoroacetylpiperazine

Product 1

HCID 8064221-AllylpiperazineYield 155.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2,2,2-trifluoro-1-piperazin-1-yl-ethanone (515 mg, 2.83 mmol) in dry CH3CN (6 mL) was added allyl bromide (0.32 mL, 3.7 mmol) and powdered potassium carbonate (0.78 g, 5.65 mmol) and the mixture stirred overnight. The reaction was concentrated under reduced pressure, diluted with CH2Cl2 (30 mL) and water (30 mL) and the aqueous layer extracted with CH2Cl2 (2×20 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford the crude di-protected piperazine (0.554 g) which was used without further purification in the next reaction.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additiondiluted with CH2Cl2 (30 mL) and water (30 mL)
  3. extractionthe aqueous layer extracted with CH2Cl2 (2×20 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32ee4c940d754b23bf862be162c61ba9
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Linked notes

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